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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Pages o3350-o3351
https://doi.org/10.1107/S1600536810048932

10-Methyl­isoalloxazine 5-oxide from synchrotron powder diffraction data

Jan Rohlíček,a* Radek Cibulka,b Jana Cibulková,c Jaroslav Maixnerc and Michal Hušáka

aDepartment of Solid State Chemistry, Institute of Chemical Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic, bDepartment of Organic Chemistry, Institute of Chemical Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic, and cCentral Laboratories, Institute of Chemical Technology in Prague, Technická 5, 166 28 Prague 6, Czech Republic
*Correspondence e-mail: rohlicej@vscht.cz

(Received 16 November 2010; accepted 23 November 2010; online 27 November 2010)

The title compound [systematic name: 10-methyl­benzo[g]pteridine-2,4(3H,10H)-dione 5-oxide], C11H8N4O3, consists of a large rigid isoalloxazine group which is approximately planar (r.m.s. deviation = 0.037 Å). In the crystal, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers. Dimers related by translation along the c axis form stacks through π–π inter­actions [centroid–centroid distances = 3.560 (5) and 3.542 (5) Å]. Weak inter­molecular C—H⋯O inter­actions further consolidate the crystal packing.

Related literature

For the preparation of the title compound, see: Yoneda et al. (1976[Yoneda, F., Sakuma, Y., Ichiba, M. & Shinomura, K. (1976). J. Am. Chem. Soc. 98, 830-835.]). For background to flavins, see: Massey (2000[Massey, V. (2000). Biochem. Soc. Trans. 28, 283-296.]), Palfey & Massey (1998[Palfey, B. & Massey, V. (1998). Comprehensive Biological Catalysis, Vol. 3, edited by M. Sinnott, pp. 83-154. London: Academic Press.]); Müller (1991[Müller, F. (1991). Chemistry and Biochemistry of Flavoenzymes. Boca Raton, Florida: CRC Press.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the crystal structures of similar compounds, see: Wang & Fritchie (1973[Wang, M. & Fritchie, C. J. (1973). Acta Cryst. B29, 2040-2045.]); Farrán et al. (2007[Farrán, M. A., Claramunt, R. M., López, C., Pinilla, E., Torres, M. R. & Elguero, J. (2007). ARKIVOC, IV, 20-38.]).

[Scheme 1]

Experimental

Crystal data

  • C11H8N4O3

  • Mr = 244.21

  • Monoclinic, P 21 /a

  • a = 13.8774 (6) Å

  • b = 14.5321 (4) Å

  • c = 4.9305 (2) Å

  • β = 90.830 (3)°

  • V = 994.22 (5) Å3

  • Z = 4

  • Synchrotron radiation

  • λ = 0.8856 Å

  • μ = 0.20 mm−1

  • T = 293 K

  • cylinder, 20 × 1 mm
Data collection

  • ESRF Grenoble, BM20 diffractometer

  • Specimen mounting: capilary

  • Data collection mode: transmission

  • Scan method: step

  • 2θmin = 4.0°, 2θmax = 36.5°, 2θstep = 0.01°
Refinement

  • Rp = 0.042

  • Rwp = 0.056

  • Rexp = 0.021

  • RBragg = 0.06

  • R(F2) = 0.060

  • χ2 = 7.129

  • 3251 data points

  • 73 parameters

  • 57 restraints

  • H-atom parameters not refined

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H1N3⋯O11i 0.86 1.92 2.764 (14) 166
C14—H2C14⋯O12ii 0.95 2.63 3.097 (16) 111
C14—H1C14⋯O13iii 0.95 2.33 3.194 (17) 151
Symmetry codes: (i) -x, -y, -z+3; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+2]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+1].

Data collection: ESRF SPEC (Certified Scientific Software, 2003[Certified Scientific Software (2003). ESRF SPEC. Certified Scientific Software, Cambridge, MA, USA.]); cell refinement: GSAS (Larson & Von Dreele, 1994[Larson, A. C. & Von Dreele, R. B. (1994). GSAS. Report LAUR 86-748. Los Alamos National Laboratory, New Mexico, USA.]); data reduction: CRYSFIRE (Shirley, 2000[Shirley, R. (2000). CRYSFIRE User's Manual. Guildford, England: The Lattice Press.]); program(s) used to solve structure: FOX (Favre-Nicolin & Černý, 2002[Favre-Nicolin, V. & Černý, R. (2002). J. Appl. Cryst. 35, 734-743.]); program(s) used to refine structure: GSAS; molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810048932/cv5002sup1.cif

Rietveld powder data: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048932/cv5002Isup2.rtv

checkCIF report


Comment top

The titled compound, 10-methylbenzo[g]pteridine-2,4(3H,10H)-dione-5-oxide belongs to a group of isoalloxazine-5-oxides which are important intermediates in synthesis of flavin derivatives (Yoneda et al., 1976). Flavins are important natural compounds which act as cofactors in redox enzymes (Massey, 2000; Palfey & Massey, 1998; Müller, 1991). Synthetic procedure utilizing isoalloxazine-5-oxides allows synthesis of non-natural flavin derivatives which are used in flavoenzyme models. To our knowledge, no crystal structure of any isoalloxazine-5-oxide has so far been published.

The asymmetric unit contains one molecule of the title compound, which is almost planar. The molecule consists of a isoalloxazine group which is formed by three connected rings - benzene, pyrazine and uracil ring. The most significant deviation from planarity occurs at the uracil ring, where the oxygen atom O12 is found to be out of the plane (torsion angle C10a—C4a—C4—O12 is app. 6.5°). The deviation of O12 atom is in accordance with the C4 carbon atom position which is slightly out of the plane and form the planar sp2 hybridization. The next deviation from planarity is on the pyrazine ring where the nitrogen atom N10 leaves out of the plane and the connected methyl group follow the direction of sp2 hybridization (torsion angle C4a—C10a—N10—C14 is app. 5.5°). Molecules of titled compound are connected together by several hydrogen bonds (Table 2) and by π-π interactions (Table 1). The strongest hydrogen bond N3-H1N3···O11 connects always two molecules together into dimers, see Fig. 2. On the other hand, the other two hydrogen bonds C14-H1C14···O13 and C14-H2C14···O12 together with π-π interactions form molecules to the infinity layers which are parallel to (100). These layers are connected by the above mentioned N3-H1N3···O11 hydrogen bonds.

The survey in the CSD (Allen, 2002) found several crystal structures of similar molecules which are derived from isoalloxazine, but no crystal structure of isoalloxazine-5-oxide which we present here was found. The similar crystal structures of 10-Methylisoalloxazine (Wang & Fritchie, 1973) and 7,10-Dimethylisoalloxazine (Farrán et al., 2007) can be used for comparison. In both structures the isoalloxazine part is approximately planar and both structures form dimers which are connected by N—H···O hydrogen bonds. The occurrence of the π-π stacking is also evident.

Related literature top

For the preparation of the title compound, see: Yoneda et al. (1976). For background to flavins, see: Massey (2000), Palfey & Massey (1998); Müller (1991). For a description of the Cambridge Structural Database, see: Allen (2002). For the crystal structures of similar compounds, see: Wang & Fritchie (1973); Farrán et al. (2007). CW Profile function number 4 with 21 terms

Experimental top

The title compound was prepared according to Yoneda et al. (1976). The 6-(N-Methylanilino)uracil (15.6 g; 65 mmol) was dissolved in acetic acid (130 ml) and sodium nitrite (22.8 g, 0.325 mol) was added. The mixture was stirred at room temperature for 3 h, diluted with water (325 ml), and allowed to stand overnight. The crystals were collected by filtration, washed with water several times, and dried. Recrystallization from aqueous acetic acid gave orange needles (17.4 g; 98%). M.p. >300 °C.

1H NMR (DMSO-d6, 300 MHz) δ3,89 (s, 3H, –CH3), 7,57 (m, 1H, Ar—H), 7.95 (m, 2H, Ar—H), 8,30 (d, 1H, J=8.2, Ar—H), 11.11 (s, 1H, NH).

For C11H8N4O3 (244.21) calculated: 54.10% C, 3.30% H, 22.94% N; found: 54.18% C, 3.41% H, 23.05% N.

The X-Ray diffraction data were collected on the Rossendorf Beamline BM20 at the ESRF in Grenoble. The energy was fixed at 14 keV which is equal to λ=0.8856 Å wavelength (the precise wavelength value was confirmed by the LaB6 standard measurement). The beamline was equipped with double-crystal Si(111) monochromator and with two collimating/focusing mirrors (Si and Pt-coating). The sample was placed in the 1-mm-borosilicate glass capillary rotated during the measurement. The diffraction pattern was measured at room temperature from 4° 2θ to 36.5° 2θ with the 0.01° 2θ step size.

Refinement top

The indexation was performed by the CRYSFIRE package (Shirley, 2000). The final cell a=13.8774 (6) Å, b = 14.5321 (4) Å, c = 4.9305 (2) Å, β = 90.830 (3) ° and V = 993.48 (7) Å3 was found from 20 peaks by several embedded indexation programs. If the volume of the molecule is compared with the volume of the found unit, it is clear that there are four molecules in the unit cell. The space group P21/a (Z = 4) was selected according to the peak extinction and the agreement of the Le-bail fit. The crystal structure was solved by parallel tempering algorithm implemented in the program FOX (Favre-Nicolin & Černý, 2002). We decided to test the structure solution run for other space groups which had similar peak extinction to validate the selection of the P21/a space group. These two space groups P 2/m and P21/m were selected, but the solution was not found.

The final refinement was performed with GSAS (Larson & Von Dreele, 1994). The structure was restrained by soft bonds and angles restraints. Four planar groups restraints were added - one for the benzene ring (C5a—C9a) and remaining three for the sp2 hybridization (C2/N1/N3/O11, C4a/C4/N3/O12 and C10a/C4a/C4/N5). At the final stage, positions and isotropic thermal parameters of all non-hydrogen atoms were refined to the low agreement R-factors (Rp = 4.2%, Rwp = 5.6%). During the refinement all hydrogen atoms were kept in their theoretical positions and were not refined. The final Rietveld plot is shown on the Fig. 3.

Structure description top

The titled compound, 10-methylbenzo[g]pteridine-2,4(3H,10H)-dione-5-oxide belongs to a group of isoalloxazine-5-oxides which are important intermediates in synthesis of flavin derivatives (Yoneda et al., 1976). Flavins are important natural compounds which act as cofactors in redox enzymes (Massey, 2000; Palfey & Massey, 1998; Müller, 1991). Synthetic procedure utilizing isoalloxazine-5-oxides allows synthesis of non-natural flavin derivatives which are used in flavoenzyme models. To our knowledge, no crystal structure of any isoalloxazine-5-oxide has so far been published.

The asymmetric unit contains one molecule of the title compound, which is almost planar. The molecule consists of a isoalloxazine group which is formed by three connected rings - benzene, pyrazine and uracil ring. The most significant deviation from planarity occurs at the uracil ring, where the oxygen atom O12 is found to be out of the plane (torsion angle C10a—C4a—C4—O12 is app. 6.5°). The deviation of O12 atom is in accordance with the C4 carbon atom position which is slightly out of the plane and form the planar sp2 hybridization. The next deviation from planarity is on the pyrazine ring where the nitrogen atom N10 leaves out of the plane and the connected methyl group follow the direction of sp2 hybridization (torsion angle C4a—C10a—N10—C14 is app. 5.5°). Molecules of titled compound are connected together by several hydrogen bonds (Table 2) and by π-π interactions (Table 1). The strongest hydrogen bond N3-H1N3···O11 connects always two molecules together into dimers, see Fig. 2. On the other hand, the other two hydrogen bonds C14-H1C14···O13 and C14-H2C14···O12 together with π-π interactions form molecules to the infinity layers which are parallel to (100). These layers are connected by the above mentioned N3-H1N3···O11 hydrogen bonds.

The survey in the CSD (Allen, 2002) found several crystal structures of similar molecules which are derived from isoalloxazine, but no crystal structure of isoalloxazine-5-oxide which we present here was found. The similar crystal structures of 10-Methylisoalloxazine (Wang & Fritchie, 1973) and 7,10-Dimethylisoalloxazine (Farrán et al., 2007) can be used for comparison. In both structures the isoalloxazine part is approximately planar and both structures form dimers which are connected by N—H···O hydrogen bonds. The occurrence of the π-π stacking is also evident.

For the preparation of the title compound, see: Yoneda et al. (1976). For background to flavins, see: Massey (2000), Palfey & Massey (1998); Müller (1991). For a description of the Cambridge Structural Database, see: Allen (2002). For the crystal structures of similar compounds, see: Wang & Fritchie (1973); Farrán et al. (2007). CW Profile function number 4 with 21 terms

Computing details top

Data collection: ESRF SPEC (Certified Scientific Software, 2003); cell refinement: GSAS (Larson & Von Dreele, 1994); data reduction: CRYSFIRE (Shirley, 2000); program(s) used to solve structure: FOX (Favre-Nicolin & Černý, 2002); program(s) used to refine structure: GSAS (Larson & Von Dreele, 1994); molecular graphics: Mercury (Macrae et al., 2006) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. ORTEP plot of the title molecule with the displacement ellipsoids drawn at the 50% probability level. The H atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. View of N—H···O hydrogen bonded (dotted lines) centrosymmetric dimers in the title crystal structure.
[Figure 3] Fig. 3. The final Rietveld plot showing the measured data (black thin-cross), calculated data (red line) and difference curve (blue line). Calculated positions of the reflection are shown by vertical bars.
10-methylbenzo[g]pteridine-2,4(3H,10H)-dione 5-oxide top
Crystal data top
C11H8N4O3Z = 4
Mr = 244.21F(000) = 504
Monoclinic, P21/aDx = 1.633 Mg m−3
Hall symbol: -P 2yabSynchrotron radiation, λ = 0.8856 Å
a = 13.8774 (6) ŵ = 0.20 mm−1
b = 14.5321 (4) ÅT = 293 K
c = 4.9305 (2) Åyellow
β = 90.830 (3)°cylinder, 20 × 1 mm
V = 994.22 (5) Å3
Data collection top
ESRF Grenoble, BM20
diffractometer		Data collection mode: transmission
Radiation source: synchrotronScan method: step
Specimen mounting: capilary2θmin = 4.0°, 2θmax = 36.5°, 2θstep = 0.01°
Refinement top
Least-squares matrix: full73 parameters
Rp = 0.04257 restraints
Rwp = 0.0560 constraints
Rexp = 0.021Hydrogen site location: inferred from neighbouring sites
RBragg = 0.06H-atom parameters not refined
R(F2) = 0.06000Weighting scheme based on measured s.u.'s
3251 data points(Δ/σ)max = 0.02
Excluded region(s): noneBackground function: GSAS Background function number 1 with 20 terms. Shifted Chebyshev function of 1st kind 1: 1199.79 2: -234.522 3: -315.536 4: 152.956 5: 123.532 6: -246.657 7: 116.810 8: 83.9272 9: -107.809 10: -12.4938 11: 79.2500 12: -25.2804 13: -27.8174 14: 13.6120 15: 6.03858 16: -3.86487 17: 2.09281 18: 9.92947 19: -18.6000 20: 1.36657
Profile function: CW Profile function number 4 with 21 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Microstrain broadening by P.W. Stephens, (1999). J. Appl. Cryst.,32,281-289. #1(GU) = 118.875 #2(GV) = 80.014 #3(GW) = 0.010 #4(GP) = 0.000 #5(LX) = 1.385 #6(ptec) = 0.00 #7(trns) = 0.00 #8(shft) = 0.0000 #9(sfec) = 0.00 #10(S/L) = 0.0005 #11(H/L) = 0.0142 #12(eta) = 0.0000 #13(S400 ) = 1.7E-01 #14(S040 ) = 1.8E-02 #15(S004 ) = 6.2E-01 #16(S220 ) = -4.6E-02 #17(S202 ) = 3.4E-01 #18(S022 ) = 1.6E-01 #19(S301 ) = -5.6E-01 #20(S103 ) = 7.9E-01 #21(S121 ) = 7.0E-02 Peak tails are ignored where the intensity is below 0.0001 times the peak Aniso. broadening axis 0.0 0.0 1.0Preferred orientation correction: March-Dollase AXIS 1 Ratio= 0.89956 h= 0.000 k= 0.000 l= 1.000 Prefered orientation correction range: Min= 0.85318, Max= 1.37377
Crystal data top
C11H8N4O3V = 994.22 (5) Å3
Mr = 244.21Z = 4
Monoclinic, P21/aSynchrotron radiation, λ = 0.8856 Å
a = 13.8774 (6) ŵ = 0.20 mm−1
b = 14.5321 (4) ÅT = 293 K
c = 4.9305 (2) Åcylinder, 20 × 1 mm
β = 90.830 (3)°
Data collection top
ESRF Grenoble, BM20
diffractometer		Scan method: step
Specimen mounting: capilary2θmin = 4.0°, 2θmax = 36.5°, 2θstep = 0.01°
Data collection mode: transmission
Refinement top
Rp = 0.0423251 data points
Rwp = 0.05673 parameters
Rexp = 0.02157 restraints
RBragg = 0.06H-atom parameters not refined
R(F2) = 0.06000
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.0773 (7)0.1443 (5)1.0053 (18)0.036 (6)*
C20.0483 (8)0.0827 (7)1.194 (3)0.075 (8)*
N30.0977 (7)−0.0028 (6)1.2303 (19)0.068 (6)*
C40.1784 (5)−0.0297 (5)1.0946 (14)0.028 (8)*
C4a0.2075 (5)0.0367 (5)0.8768 (14)0.049 (7)*
N50.2843 (7)0.0175 (6)0.725 (2)0.120 (8)*
C5a0.3110 (6)0.0833 (6)0.5319 (18)0.077 (9)*
C60.3917 (7)0.0645 (6)0.365 (2)0.037 (7)*
C70.4210 (6)0.1290 (8)0.180 (2)0.052 (7)*
C80.3703 (8)0.2112 (7)0.1520 (18)0.059 (8)*
C90.2917 (7)0.2332 (6)0.311 (2)0.054 (8)*
C9a0.2610 (6)0.1684 (6)0.5019 (18)0.045 (9)*
N100.1787 (7)0.1824 (7)0.6664 (19)0.078 (7)*
C10a0.1522 (5)0.1216 (5)0.8572 (14)0.046 (8)*
O11−0.0238 (7)0.1000 (7)1.338 (2)0.063 (5)*
O120.2230 (7)−0.1014 (5)1.1524 (17)0.037 (4)*
O130.3291 (8)−0.0597 (7)0.748 (2)0.100 (5)*
C140.1211 (10)0.2660 (9)0.619 (3)0.095 (9)*
H1N30.0746−0.04051.34660.0804*
H1C60.4250.00760.38160.0456*
H1C70.47580.11730.07180.0612*
H1C80.39060.2540.01880.0708*
H1C90.25970.29050.29010.0636*
H1C140.14880.30130.4790.114*
H2C140.1190.30130.7810.114*
H3C140.0570.2490.5670.114*
Geometric parameters (Å, º) top
O11—C21.261 (16)N10—C9a1.425 (13)
C4—C4a1.503 (10)N3—C21.429 (14)
O12—C41.243 (11)N3—C41.370 (12)
C5a—C9a1.425 (12)N5—C5a1.403 (13)
O13—N51.287 (14)N5—C4a1.341 (12)
C5a—C61.426 (13)C10a—C4a1.455 (10)
N1—C10a1.321 (12)C14—H1C140.9500
C6—C71.374 (14)C14—H2C140.9500
N1—C21.356 (15)C14—H3C140.9500
C7—C81.392 (15)C6—H1C60.9500
N10—C10a1.346 (12)C7—H1C70.9500
C8—C91.390 (14)N3—H1N30.8600
N10—C141.471 (17)C8—H1C80.9500
C9—C9a1.402 (13)C9—H1C90.9500
Cg1···Cg2i3.56 (1)Cg1···Cg3i3.54 (1)
C2—N1—C10A117.3 (8)C8—C9—C9A118.2 (8)
C2—N3—C4125.5 (9)N10—C9A—C5A117.3 (8)
O13—N5—C4A121.3 (9)N10—C9A—C9122.7 (8)
O13—N5—C5A121.5 (9)C5A—C9A—C9120.0 (8)
C4A—N5—C5A117.2 (8)N1—C10A—N10116.6 (8)
C9A—N10—C10A122.3 (9)N1—C10A—C4A126.4 (7)
C9A—N10—C14117.8 (9)N10—C10A—C4A117.0 (7)
C10A—N10—C14120.0 (9)C2—N3—H1N3117
O11—C2—N1120.0 (10)C4—N3—H1N3117
O11—C2—N3119.1 (11)C5A—C6—H1C6120
N1—C2—N3120.9 (10)C7—C6—H1C6120
O12—C4—N3122.4 (8)C6—C7—H1C7120
O12—C4—C4A124.3 (7)C8—C7—H1C7120
N3—C4—C4A113.3 (7)C7—C8—H1C8118
N5—C4A—C4119.3 (7)C9—C8—H1C8119
N5—C4A—C10A124.2 (7)C8—C9—H1C9121
C4—C4A—C10A116.4 (6)C9A—C9—H1C9121
N5—C5A—C6118.6 (8)N10—C14—H1C14110
N5—C5A—C9A121.9 (8)N10—C14—H2C14110
C6—C5A—C9A119.5 (8)N10—C14—H3C14109
C5A—C6—C7119.7 (8)H1C14—C14—H2C14110
C6—C7—C8119.8 (9)H1C14—C14—H3C14109
C7—C8—C9122.8 (9)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···O11ii0.861.922.764 (14)166
C14—H2C14···O12iii0.952.633.097 (16)111
C14—H1C14···O13iv0.952.333.194 (17)151
Symmetry codes: (ii) −x, −y, −z+3; (iii) −x+1/2, y+1/2, −z+2; (iv) −x+1/2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC11H8N4O3
Mr244.21
Crystal system, space groupMonoclinic, P21/a
Temperature (K)293
a, b, c (Å)13.8774 (6), 14.5321 (4), 4.9305 (2)
β (°) 90.830 (3)
V (Å3)994.22 (5)
Z4
Radiation typeSynchrotron, λ = 0.8856 Å
µ (mm−1)0.20
Specimen shape, size (mm)Cylinder, 20 × 1
Data collection
DiffractometerESRF Grenoble, BM20
Specimen mountingCapilary
Data collection modeTransmission
Scan methodStep
2θ values (°)2θmin = 4.0 2θmax = 36.5 2θstep = 0.01
Refinement
R factors and goodness of fitRp = 0.042, Rwp = 0.056, Rexp = 0.021, RBragg = 0.06, R(F2) = 0.06000, χ2 = 7.129
No. of parameters73
No. of restraints57
H-atom treatmentH-atom parameters not refined

Computer programs: ESRF SPEC (Certified Scientific Software, 2003), GSAS (Larson & Von Dreele, 1994), CRYSFIRE (Shirley, 2000), FOX (Favre-Nicolin & Černý, 2002), Mercury (Macrae et al., 2006) and PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H1N3···O11i0.861.922.764 (14)166
C14—H2C14···O12ii0.952.633.097 (16)111
C14—H1C14···O13iii0.952.333.194 (17)151
Symmetry codes: (i) −x, −y, −z+3; (ii) −x+1/2, y+1/2, −z+2; (iii) −x+1/2, y+1/2, −z+1.
 

Acknowledgements

We acknowledge the European Synchrotron Radiation Facility for provision of synchrotron radiation facilities for project CH-3085 and we would like to thank Dr Carsten Baehtz for assistance in using Rossendorf Beamline BM20. This study was supported by the research programs NPV II 2B08021, MSM6046137302 and MSM 6046137301 of the Ministry of Education, Youth and Sports of the Czech Republic.

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Pages o3350-o3351
https://doi.org/10.1107/S1600536810048932
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